Couldn't tell you I'm afraid, I also haven't bought it. I grabbed DR2 because I saw it really cheap on sale and just wanted a rally sim rather than seeking out a specific one
Both of the other two are wearing identical hoods, yes. The other person in the room is Astrid, the Dark Brotherhood assassin telling you to kill one of them. Vasha is definitely by far the Zorro-iest one present though
Oh, I didn't mean to come across as argumentative, I just offered a description in case it jogged a memory. It's entirely possible you never did meet him. Though if it helps at all, he's wearing an execution hood rather than an executioner's hood — as in, he's the one getting executed. You are correct that all three are wearing them and Vasha doesn't give much of a shit about the whole situation, all things considered
He's one of the three captives you can choose to kill at the start of the Dark Brotherhood questline
Elaborate pls,
The voice actor is André Sogliuzzo, who voiced Banderas' Puss in Boots from Shrek in various appearances outside of the main films and also voiced the actual character of Antonio Banderas in an episode of Celebrity Deathmatch
That's the only reference, yeah. The character is only present for one scene in one quest, and the only mention of his sexual exploits is that line. I certainly always interpreted him as a womaniser rather than a rapist
It's funny that you mention Zorro — the voice actor that does this character's lines (and also other male khajiit) has done parts to fill in for Antonio Banderas before
To be fair he may not actually be a rapist. He calls himself "defiler of daughters", but he's doing so in a theatrically rogueish list of reasons people would want to kill him, so it could just as well be consensual but the parents are furious about it.
However even if that is the case, he actually is also a self-described murderer and thief who implies that he runs a dangerous gang of some sort and regularly has people trying to kill him
Based on your enjoyment of management and strategy, Paradox's grand strategy games might be something you enjoy. Same publisher as Cities Skylines. There are four main series of them, each with their own mechanics but enough broad-scale similarities that knowing one helps with the others. They are:
Crusader Kings, set in medieval Europe, North Africa, and about half of Asia. This one is the most roleplay-heavy, as you play as a succession of characters within a feudal dynasty rather than a country
Europa Universalis, set from the European Renaissance up to the end of the Napoleonic wars. The whole world is playable, and exploration is a big mechanic
Victoria, which covers the world through the rise of industrialism. This one is the most simulation-heavy, focusing gameplay around economic development and the diplomatic manoeuvring of great powers
Hearts of Iron, which is the Second World War game. This is the one to go for if you want to play the military side of things
What distinguishes them from strategy games like Civ and Age of Empires is the greatly-reduced abstraction. There's no expectation of every starting point or playable country being balanced; if you start as Belgium in Hearts of Iron, you're going to have to do something clever to not get steamrolled by Germany. There's also no win condition beyond what you set for yourself. When I start a game of Crusader Kings, I'm not trying to win the game, I'm saying to myself "let's see if I can unite all of Britain and Ireland under a Gaelic ruler"
All Paradox games have quite a lot of DLC, but the base games are solid (often now including several of the earlier DLCs for free, in the case of older games) and they go on steep sales pretty often. If there's not a specific time period or mechanic that sways you towards one of the games, I recommend Crusader Kings 3 for the best new player experience
I'd also add that CK3 is a step above most Paradox games in terms of beginner-friendliness. Everything has a tooltip defining what it does, and most of the game-specific words in that tooltip have tooltips of their own. It's not like the older games and their "lol keep the wiki open and good fucking luck" approach to explaining themselves